Palladium-Catalyzed Carbo-Aminative Cyclization of 1,6-Enynes: Access to Napthyridinone Derivatives
Undamatla Suri Babu, Maneesh Kumar Reddy Singam, Muniganti Naveen Kumar, Jagadeesh Babu Nanubolu, Maddi Sridhar Reddy
Abstract
1,6-Enynes have recently stimulated enormous attention toward paving the way to unique cascade cyclizations offering complex cyclic motifs from linear substrates. We describe herein a general approach to napthyridinones via the Pd-catalyzed annulation of 1,6-enynes with 2-iodoanilines. This protocol represents a rare carbo-aminative annulative cyclization via the 6-endo-trig mode, subduing the well-documented exo-trig/dig cyclizations. The regioselective aryl palladation of alkyne followed by Heck-type intramolecular coupling before isomerization were key in realizing this cascade.
Topics & Concepts
ChemistryIsomerizationIntramolecular forceAnnulationPalladiumCatalysisAlkyneCascadeArylCombinatorial chemistryRegioselectivityStereochemistryOrganic chemistryAlkylChromatographyCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsCatalytic Cross-Coupling Reactions